


Learning Experience

by SpicyReyes



Category: Red Dead Redemption (Video Games)
Genre: Anal Fingering, F/M, Femdom, Prostitution, ambiguously teenage-ish arthur, sort of a prequel to The Sins
Language: English
Status: Completed
Published: 2019-06-26
Updated: 2019-06-26
Packaged: 2020-05-20 05:50:30
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,742
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19370767
Author URL: https://archiveofourown.org/users/SpicyReyes/pseuds/SpicyReyes
Summary: Best four dollars he ever spent.





	Learning Experience

**Author's Note:**

> this is part of the arthur backstory that will be canon in my other fic so uh....enjoy kids

Really, he asked on accident. 

He’d thought about it, once or twice, when a comment had implied it- had thought about it in a different context late at night, left to his own imagination.

But he hadn’t meant to  _ ask.  _

The prostitute who approached them gave an elegant red-lipped smile, leaned up against Dutch’s side.

“You sure, sweetheart?” she cooed. “Cut you a deal?” She took his hand in her own, guiding it to her breast. “Start from a dollar,” she said, guiding the hand down then, bringing it to rest on her ass. “All the way up to five.” She winked. “That ain’t for the front, mind. That’s only three.”

Arthur couldn’t help it, couldn’t have stopped it coming out of his mouth even if he’d known it was going to. “How y’all do that?” he asked. “Cain’t feel  _ good,  _ surely.”

“You’d be surprised, honey,” the woman purred, her attention now on him. “A lil’ Vaseline and a lovin’ touch’ll getcha far.” 

_ “Vaseline?” _

She removed herself from Dutch’s side, coming instead to perch on his knee, hand dragging down his chest. “Five dollars, boy,” she prompted him. “Pay it and I’ll be happy to show ya.”

Hosea was going to kill him for it, but damn if he didn’t want to know. 

“Alright,” Arthur agreed. He firmly ignored Dutch’s amusement, and took the woman’s hand, letting her lead him off toward a room.

Soon, he was being backed into a bed, straddled by a woman with her skirt hiked up, leaning in close like she was about to kiss him.

“Now, honey,” she said, hand trailing down his chest. “You had a woman before?”

“I ain’t a kid,” Arthur said.

The woman let out a titter. “Just a boy,” she teased. “How old are you, son? Sixteen? Seventeen?” 

“Does it matter?”

She tipped her head back with a laugh. “Oh, I like you,” she said. “I guess it don’t. Tell me, though…” Her fingertips drummed on his chest. “Do you want me to teach you how to  _ do  _ it,” she said, before lowering a hand, sliding it first from Arthur’s thigh to come around and rest against his ass. “Or show you how to take it?”

Arthur blanched.

“Aw, don’t look so worried, sweetie,” the woman said. “I mighta seen right through ya, but I know what I’m lookin’ for. Most’ll look right past it.”

“...You ain’t gonna say nothin’?” Arthur said. He’d wanted it to be a demand, but it came out a strained question instead. 

“Not a word,” she assured him. “But I asked a question, and I’m gonna need an answer, sugar.”

Arthur’s lips pressed tight into a thin, blanched white line. 

“Takin’, then,” she said, a wry amused smile on her face. “I was hopin’ it would be. Don’t get the chance to play too much...I’ll drop ya a dollar down for the pleasure, even.” She grabbed his belt buckle, tapping the metal with a fingernail. “Strip down, baby.”

She climbed off him, watching almost hungrily as he followed her instructions, petting his thigh when he was done. 

“Good, good,” she said, before patting the inside of his thigh with the back of her hand. “Pull your knees up.”

Feeling highly exposed, Arthur did so, flushing red when the woman praised another  _ “good”  _ and further nudged his feet apart. 

“I could have you on your belly,” she said. “That’d make it easier...but if you learn it this way, you can do it any way.” 

She reached into the neckline of her dress, fishing something out of the bodice, pulling free a tiny metal tin.

“Here’s the secret,” she said, popping it open, before dipping a finger deep into the tin and pulling it out well coated in thick gel. She toyed with her fingers in the air, spreading the substance evenly across her middle three fingers. “The more ya got, the less you feel. Use as much as you can fit when you start, but find your balance. You gotta get it just right - feel just enough to make it good.” 

And then she lowered her slicked hand, setting a wet finger against his asshole.

He flinched immediately, squirming again, but she didn’t say or do anything. She just held there, waiting patiently until he settled again. When he’d calmed again enough to relax a little, she smiled, and without warning, eased the tip of her finger in.

“Shit,” Arthur swore. The sensation was uncomfortable and strange, and spent a chill up his spine with the foreign nature of it all. 

As though in apology, the woman leaned forward, placing a light kiss on his lower stomach. “Shh,” she cooed to him. “The hard part’s getting it in.”

Instead of pressing further, though, she kissed lower, slowly finding her way down, until she was taking him into her mouth.

Arthur gave a very sharp inhale, followed by another swear, as the woman took his distraction as an opportunity to take her finger up to the knuckle. 

Around him came a vibration as she hummed, possibly in apology. Her head began to move, drawing back and forth, slowly coaxing the interest back out of Arthur. 

Just as he was starting to forget the alien sensation of his ass, the finger moved again. The fingertip curled a bit, then dragged slowly down, then straightened and slid slowly back in. 

It felt a bit like she was pulling him forward, pressing him further into her mouth from the inside. It brought nerves he’d never paid much mind to into motion, drawing his full attention even more than the mouth on his cock did, and he felt his breathing coming faster in response. 

The dragging motion was repeated a few times, letting him get good and comfortable with it, before she changed up again, slowly swirling it around, pressing against each side of him inside, testing the give of the muscle.

A flick of her tongue brought his attention back to his dick, and once again, his distraction was taken advantage of, another fingertip forcing itself in beside the first. 

Arthur grit his teeth, hissing out a pained breath. Another fingertip touched his hole, and he tensed, but it did not press in. Instead, it began to massage at the muscle gently from the outside, while the fingers inside resumed their gentle circling. 

The massaging helped soften the stretch of the rim of muscle being breached, and with that under control, it wasn’t too bad. The inside seemed much more willing to part for her, the further in it went, and soon, he was relaxing again, arching into her touch as he’d been before.

He thought he could see, now, how men tolerated doing this to one another. He could see himself allowing someone to do this to him, if he thought he’d be given some satisfaction in return, whether by a hand in the moment or by being allowed to do the same after.

Just when he thought he’d had it figured out, and was simply relaxing back, enjoying the mouth on his cock and letting the other touches become tactile white noise, the fingers curled together, and a spark of pleasure shot through him.

“Oh,” Arthur gasped, hips jerking a bit in response. The woman gave a satisfied hum around him in reply, and did it again. 

She split her fingers within him, widening them out, curling them again. These seemed to brush just shy of the right spot, as though passing over the sides, leaving him shivering but dissatisfied. He found himself bearing down, hips wriggling as he tried to force the angle back. 

The lips pulled off him with a gentle laugh, drawing a frustrated whine from him. 

“There we go,” she said, and turned her hand a bit to the side, changing up the angle as she moved her fingers again, sending that shock through him again. She spun her fingers a couple of times, then pulled back, swiveling them lower down, so that his rim was being stretched further. Each time it would start to twinge, though, she would plunge back in, fingertips grazing deliciously stimulating nerves. 

When she added the third finger, she didn’t even have to distract him with her mouth again. Instead, she returned to placing teasing kisses along his stomach and inner thighs, avoiding the center entirely, instead getting Arthur twisting and panting from her ministrations inside him. 

“You’re pretty good at this,” she said, light and teasing. “Tiny little thing like you…you’ll be popular in the right crowds, sweetheart.” She grinned up at him. “Looks like you’ll be having fun, too...some men like a little of this, but you seem to like it a  _ lot.”  _

Arthur flushed cherry red, but couldn’t stop himself still keening at her touch. 

She pressed her fingers tight together, and pulled them halfway from him, before pushing right back in, straight up into the good spot inside. 

That’s what a cock would feel like, Arthur realized, as she began to do it again and again, hitting that spot each time. If he were fucking a man - if a man were fucking  _ him -  _ that’s what it would feel like. That would be a man’s cock dragging across his rim, slamming in deep, pressing up against a set of wondrous nerves. That would be a man’s hand on his thigh, holding his leg out of the way, that’d be-... _ oh. _

Arthur let out a soft cry as he came, arching hard into the touch. 

“There’s a good boy,” the prostitute murmured. Her fingers drew slowly out of him, the knuckles popping free making him wince, and drew her clean hand over his chest, gently petting. “You took that real nice. You definitely inverted as hell, but I think you’ll be just fine.” She leaned down, placing a kiss against his cheek, before she pushed back, standing to leave casually. 

“Won’t say a word,” she promised again, and reached down for his pants, digging herself four dollars and shooting him a wink. “You should practice that a few times before you go after the real thing, honey,” she advised, and tossed the Vaseline tin onto the bed. “I’ll leave you this to get ya started.” She moved around the bed, pecked his cheek again, and turned to leave. “This was fun, sweetie. See you some other time, hm?”

“Yeah,” Arthur breathed out, finally finding his voice, boneless and dazed on the bed. “Yeah...Okay.”


End file.
